2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-16-phenyl-PGF compounds

ABSTRACT

The present invention relates to novel 2-decarboxy-2-aminomethyl-9-deoxy-9-methylene-16-phenyl-PGF compounds. These compounds are useful pharmacological agents, and are useful for the same purposes as the corresponding PGE-type compounds.

CROSS REFERENCE TO RELATED APPLICATIONS

This application is a continuation-in-part of Ser. No. 786,249, filed Apr. 11, 1977, issued as U.S. Pat. No. 4,118,584 on Oct. 3, 1978.

The present invention relates to novel 2-decarboxy-2-aminomethyl-9-deoxy-9-methylene-16-phenyl-PGF compounds, the essential material constituting a disclosure of which is incorporated here by reference from U.S. Pat. No. 4,118,584. 

I claim:
 1. A prostaglandin analog of the formula ##STR1## wherein Y₁ is trans-CH═CH--, --C.tbd.C--, or --CH₂ CH₂ --;wherein M₁ is ##STR2## wherein R₅ is hydrogen or methyl; wherein L₁ is ##STR3## wherein R₃ and R₄ are hydrogen, methyl, or fluoro, being the same or different, with the proviso that one of R₃ and R₄ is fluoro only when the other is hydrogen or fluoro; wherein Z₁ is (1) cis--CH═CH--CH₂ --(CH₂)_(g) --CH₂ --, (2) cis--CH═CH--CH₂ --(CH₂)_(g) --CF₂ --, (3) cis--CH₂ --CH═CH--(CH₂)_(g) --CH₂ --, (4) --(CH₂)₃ --(CH₂)_(g) --CH₂ --, (5) --(CH₂)₃ --(CH₂)_(g) --CF₂ --, (6) --CH₂ --O--CH₂ --(CH₂)_(g) --CH₂ --, (7) --C.tbd.C--CH₂ --(CH₂)_(g) --CH₂ --, (8) --CH₂ --C.tbd.C--(CH₂)_(g) --CH₂ --, ##STR4## wherein g is one, 2, or 3; wherein T is chloro, fluoro, trifluoromethyl, alkyl of one to 3 carbon atoms, inclusive, or alkoxy of one to 3 carbon atoms, inclusive, and s is zero, one, 2, or 3, the various T's being the same or different, with the proviso that not more than two T's are other than alkyl;wherein L₂ and L₃ are hydrogen, or alkyl of one to 4 carbon atoms, inclusive.
 2. A prostaglandin analog according to claim 1, wherein Y₁ is --CH₂ CH₂ --.
 3. A prostaglandin analog according to claim 2, wherein ##STR5##
 4. A prostaglandin analog according to claim 2, wherein ##STR6##
 5. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-3,7-inter-m-phenylene-3-oxa-16-phenyl-4,5,6,17,18,19,20-heptanor-13,14-dihydro-PGF₁, a prostaglandin analog according to claim
 4. 6. A prostaglandin analog according to claim 2, wherein Z₁ is cis--CH₂ --CH═CH--(CH₂)_(g) --CH₂ --.
 7. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-cis-3,4-didehydro-16-phenyl-17,18,19,20-tetranor-13,14-dihydro-PGF₁, a prostaglandin analog according to claim
 6. 8. A prostaglandin analog according to claim 2, wherein Z₁ is --CH₂ --O--CH₂ --(CH₂)_(g) --CH₂ --.
 9. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-5-oxa-16-phenyl-17,18,19,20-tetranor-13,14-dihydro-PGF₁, a prostaglandin analog according to claim
 8. 10. A prostaglandin analog according to claim 2, wherein Z₁ is --C.tbd.C--CH₂ --(CH₂)_(g) --CH₂ --.
 11. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-5,6-didehydro-16-phenyl-17,18,19,20-tetranor-13,14-dihydro-PGF₂, a prostaglandin analog according to claim
 10. 12. A prostaglandin analog according to claim 2, wherein Z₁ is --CH₂ --C.tbd.C--(CH₂)_(g) --CH₂ --.
 13. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-4,4,5,5-tetradehydro-16-phenyl-17,18,19,20-tetranor-13,14-dihydro-PGF₁, a prostaglandin analog according to claim
 12. 14. A prostaglandin analog according to claim 2, wherein Z₁ is --(CH₂)₃ --(CH₂)_(g) --CH₂ --.
 15. A prostaglandin analog according to claim 14, wherein M₁ is ##STR7##
 16. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-15-epi-16-phenyl-17,18,19,20-tetranor-13,14-dihydro-PGF₁, a prostaglandin analog according to claim
 15. 17. A prostaglandin analog according to claim 14, wherein M₁ is ##STR8##
 18. A prostaglandin analog according to claim 17, wherein s is zero or one and T is chloro, fluoro, or trifluoromethyl.
 19. A prostaglandin analog according to claim 18, wherein g is
 3. 20. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-2a,2b-dihomo-15-methyl-16-phenyl-17,18,19,20-tetranor-13,14-dihydro-PGF₁, a prostaglandin analog according to claim
 19. 21. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-2a,2b-dihomo-16-phenyl-17,18,19,20-tetranor-13,14-dihydro-PGF₁, a prostaglandin analog according to claim
 19. 22. A prostaglandin analog according to claim 18, wherein g is one.
 23. A prostaglandin analog according to claim 22, wherein at least one of R₃ and R₄ is methyl.
 24. A prostaglandin analog according to claim 23, wherein R₃ and R₄ are both methyl.
 25. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-16-methyl-16-phenyl-18,19,20-trinor-13,14-dihydro-PGF₁, a prostaglandin analog according to claim
 24. 26. A prostaglandin analog according to claim 22, wherein at least one of R₃ and R₄ is fluoro.
 27. A prostaglandin analog according to claim 26, wherein R₃ and R₄ are both fluoro.
 28. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-16,16-difluoro-16-phenyl-17,18,19,20-tetranor-13,14-dihydro-PGF₁, a prostaglandin analog according to claim
 27. 29. A prostaglandin analog according to claim 22, wherein R₃ and R₄ are both hydrogen.
 30. A prostaglandin analog according to claim 29, wherein R₅ is methyl.
 31. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-15-methyl-16-phenyl-17,18,19,20-tetranor-13,14-dihydro-PGF₁, a prostaglandin analog according to claim
 30. 32. A prostaglandin analog according to claim 29, wherein R₅ is hydrogen.
 33. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-16-phenyl-17,18,19,20-tetranor-13,14-dihydro-PGF₁, a prostaglandin analog according to claim
 32. 34. A prostaglandin analog according to claim 2, wherein Z₁ is cis--CH═CH--CH₂ --(CH₂)_(g) --CH₂ --.
 35. A prostaglandin analog according to claim 34, wherein M₁ is ##STR9##
 36. A prostaglandin analog according to claim 35, wherein s is zero or one and T is chloro, fluoro, or trifluoromethyl.
 37. A prostaglandin analog according to claim 36, wherein g is
 3. 38. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-2a,2b-dihomo-15-epi-15-methyl-16-phenyl-17,18,19,20-tetranor-13,14-dihydro-PGF₂, a prostaglandin analog according to claim
 37. 39. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-2a,2b-dihomo-15-epi-16-phenyl-17,18,19,20-tetranor-13,14-dihydro-PGF.sub.2, a prostaglandin analog according to claim
 37. 40. A prostaglandin analog according to claim 36, wherein g is one.
 41. A prostaglandin analog according to claim 40, wherein at least one of R₃ and R₄ is methyl.
 42. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-15-epi-16-methyl-16-phenyl-18,19,20-trinor-13,14-dihydro-PGF₂, a prostaglandin analog according to claim
 41. 43. A prostaglandin analog according to claim 40, wherein at least one of R₃ and R₄ is fluoro.
 44. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-15-epi-16,16-difluoro-16-phenyl-17,18,19,20-tetranor-13,14-dihydro-PGF₂, a prostaglandin analog according to claim
 43. 45. A prostaglandin analog according to claim 40, wherein R₃ and R₄ are both hydrogen.
 46. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-15-epi-16-methyl-16-phenyl-17,18,19,20-tetranor-13,14-dihydro-PGF₂, a prostaglandin analog according to claim
 45. 47. A prostaglandin analog according to claim 34, wherein M₁ is ##STR10##
 48. A prostaglandin analog according to claim 47, wherein s is zero and T is chloro, fluoro, trifluoromethyl.
 49. A prostaglandin analog according to claim 48, wherein g is
 3. 50. A prostaglandin analog according to claim 49, wherein at least one of R₃ and R₄ is methyl.
 51. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-2a,2b-dihomo-16-methyl-16-phenyl-18,19,20-trinor-13,14-dihydro-PGF₂, a prostaglandin analog according to claim
 50. 52. A prostaglandin analog according to claim 49, wherein at least one of R₃ and R₄ is fluoro.
 53. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-2a,2b-dihomo-16,16-difluoro-16-phenyl-17,18,19,20-tetranor-13,14-dihydro-PGF₂, a prostaglandin analog according to claim
 52. 54. A prostaglandin analog according to claim 49, wherein R₃ and R₄ are both hydrogen.
 55. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-2a,2b-dihomo-16-phenyl-17,18,19,20-tetranor-13,14-dihydro-PGF₂, a prostaglandin analog according to claim
 54. 56. A prostaglandin analog according to claim 38, wherein g is one.
 57. A prostaglandin analog according to claim 56, wherein at least one of R₃ and R₄ is methyl.
 58. A prostaglandin analog according to claim 57, wherein R₃ and R₄ are both methyl.
 59. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-16-methyl-16-phenyl-18,19,20-trinor-13,14-dihydro-PGF₂, a prostaglandin analog analog according to claim
 58. 60. A prostaglandin analog according to claim according to claim 56, wherein at least one of R₃ and R₄ is fluoro.
 61. A prostaglandin analog according to claim 60, wherein R₃ and R₄ are both fluoro.
 62. A prostaglandin analog according to claim 61, wherein R₅ is methyl.
 63. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-15-methyl-16,16-difluoro-16-phenyl-17,18,19,20-tetranor-13,14-dihydro-PGF₂, a prostaglandin analog according to claim
 62. 64. A prostaglandin analog according to claim 61, wherein R₅ is hydrogen.
 65. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-16,16-difluoro-16-phenyl-17,18,19,20-tetranor-13,14-dihydro-PGF₂, a prostaglandin analog according to claim
 64. 66. A prostaglandin analog according to claim 56, wherein R₃ and R₄ are both hydrogen.
 67. A prostaglandin analog according to claim 66, wherein R₅ is methyl.
 68. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-15-methyl-16-phenyl-17,18,19,20-tetranor-13,14-dihydro-PGF₂, a prostaglandin analog according to claim
 67. 69. A prostaglandin analog according to claim 66, wherein R₅ is hydrogen.
 70. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-16-phenyl-17,18,19,20-tetranor-13,14-dihydro-PGF₂, a prostaglandin analog according to claim
 69. 71. A prostaglandin analog according to claim 1, wherein Y₁ is --C.tbd.C--.
 72. A prostaglandin analog according to claim 71, wherein Z₁ is cis--CH═CH--CH₂ --(CH₂)_(g) --CF₂ --.
 73. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-2,2-difluoro-16-phenyl-17,18,19,20-tetranor-13,14-didehydro-PGF₂, a prostaglandin analog according to claim
 72. 74. A prostaglandin analog according to claim 71, wherein Z₁ is --(CH₂)₃ --(CH₂)_(g) --CF₂ --.
 75. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-2,2-difluoro-16-phenyl-17,18,19,20-tetranor-13,14-didehydro-PGF₁, a prostaglandin analog according to claim
 74. 76. A prostaglandin analog according to claim 71, wherein Z₁ is cis--CH₂ --CH═CH--(CH₂)_(g) --CH₂ --.
 77. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-cis-4,5-didehydro-16-phenyl-17,18,19,20-tetranor-13,14-didehydro-PGF₁, a prostaglandin analog according to claim
 76. 78. A prostaglandin analog according to claim 71, wherein Z₁ is --CH₂ --O--CH₂ --(CH₂)_(g) --CH₂ --.
 79. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-5-oxa-16-phenyl-17,18,19,20-tetranor-13,14-didehydro-PGF₁, a prostaglandin analog according to claim
 78. 80. A prostaglandin analog according to claim 71, wherein Z₁ is --C.tbd.C--CH₂ --(CH₂)_(g) --CH₂ --.
 81. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-16-phenyl-17,18,19,20-tetranor-5,6,13,14-tetradehydro-PGF₂, a prostaglandin analog according to claim
 80. 82. A prostaglandin analog according to claim 71, wherein Z₁ is --CH₂ --C.tbd.C--(CH₂)_(g) --CH₂ --.
 83. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-16-phenyl-17,18,19,20-tetranor-4,4,5,5,13,14-hexadehydro-PGF₁, a prostaglandin analog according to claim
 82. 84. A prostaglandin analog according to claim 71, wherein Z₁ is --(CH₂)₃ --(CH₂)_(g) --CH₂ --.
 85. A prostaglandin analog according to claim 84, wherein M₁ is ##STR11##
 86. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-15-epi-16-phenyl-17,18,19,20-tetranor-13,14-didehydro-PGF₁, a prostaglandin analog according to claim
 85. 87. A prostaglandin analog according to claim 84, wherein M₁ is ##STR12##
 88. A prostaglandin analog according to claim 87, wherein s is zero or one and T is chloro, fluoro, or trifluoromethyl.
 89. A prostaglandin analog according to claim 88, wherein g is
 3. 90. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-2a,2b-dihomo-15-methyl-16-phenyl-17,18,19,20-tetranor-13,14-didehydro-PGF₁, a prostaglandin analog according to claim
 89. 91. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-2a,2b-dihomo-15-methyl-16-phenyl-17,18,19,20-tetranor-13,14-didehydro-PGF₁, a prostaglandin analog according to claim
 89. 92. A prostaglandin analog according to claim 88, wherein g is one.
 93. A prostaglandin analog according to claim 92, wherein at least one of R₃ and R₄ is methyl.
 94. A prostaglandin analog according to claim 93, wherein R₃ and R₄ are both methyl.
 95. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-16-methyl-16-phenyl-18,19,20-trinor-13,14-didehydro-PGF₁, a prostaglandin analog according to claim
 94. 96. A prostaglandin analog according to claim 92, wherein at least one of R₃ and R₄ is fluoro.
 97. A prostaglandin analog according to claim 96, wherein R₃ and R₄ are both fluoro.
 98. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-16,16-difluoro-16-phenyl-17,18,19,20-tetranor-13,14-didehydro-PGF₁, a prostaglandin analog according to claim
 97. 99. A prostaglandin analog according to claim 92, wherein R₃ and R₄ are both hydrogen.
 100. A prostaglandin analog according to claim 99, wherein R₅ is methyl.
 101. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-15-methyl-16-phenyl-17,18,19,20-tetranor-13,14-didehydro-PGF₁, a prostaglandin analog according to claim
 100. 102. A prostaglandin analog according to claim 99, wherein R₅ is hydrogen.
 103. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-16-phenyl-17,18,19,20-tetranor-13,14-didehydro-PGF₁, a prostaglandin analog according to claim
 102. 104. A prostaglandin analog according to claim 71, wherein Z₁ is cis--CH═CH--CH₂ --(CH₂)_(g) --CH₂ --.
 105. A prostaglandin analog according to claim 104, wherein M₁ is ##STR13##
 106. A prostaglandin analog according to claim 105, wherein s is zero or one and T is chloro, fluoro, trifluoromethyl.
 107. A prostaglandin analog according to claim 106, wherein g is
 3. 108. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-2a,2b-dihomo-15-epi-15-methyl-16-phenyl-17,18,19,20-tetranor-13,14-didehydro-PGF₂, a prostaglandin analog according to claim
 107. 109. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-2a,2b-dihomo-15-epi-16-phenyl-17,18,19,20-tetranor-13,14-didehydro-PGF₂, a prostaglandin analog according to claim
 107. 110. A prostaglandin analog according to claim 106, wherein g is one.
 111. A prostaglandin analog according to claim 110, wherein at least one of R₃ and R₄ is methyl.
 112. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-15-epi-16-methyl-16-phenyl-18,19,20-trinor-13,14-didehydro-PGF₂, a prostaglandin analog according to claim
 111. 113. A prostaglandin analog according to claim 110, wherein at least one of R₃ and R₄ is fluoro.
 114. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-15-epi-16,16-difluoro-16-phenyl-17,18,19,20-tetranor-13,14-didehydro-PGF₂, a prostaglandin according to claim
 113. 115. A prostaglandin analog according to claim 110, wherein R₃ and R₄ are both hydrogen.
 116. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-15-epi-15-methyl-16-phenyl-17,18,19,20-tetranor-13,14-didehydro-PGF₂, a prostaglandin analog according to claim
 115. 117. A prostaglandin analog according to claim 104, wherein M₁ is ##STR14##
 118. A porstaglandin analog according to claim 117, wherein s is zero or one and T is chloro, fluoro, or trifluoromethyl.
 119. A prostaglandin analog according to claim 118, wherein g is
 3. 120. A prostaglandin analog according to claim 119, wherein at least one of R₃ and R₄ is methyl.
 121. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-2a,2b-dihomo-16-methyl-16-phenyl-18,19,20-trinor-13,14-didehydro-PGF₂, a prostaglandin analog according to claim
 120. 122. A prostaglandin analog according to claim 119, wherein at least one of R₃ and R₄ is fluoro.
 123. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-2a,2b-dihomo-16,16-difluoro-16-phenyl-17,18,19,20-tetranor-13,14-didehydro-PGF₂, a prostaglandin analog according to claim
 122. 124. A prostaglandin analog according to claim 119, wherein R₃ and R₄ are both hydrogen.
 125. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-2a,2b-dihomo-16-phenyl-17,18,19,20-tetranor-15-methyl-13,14-didehydro-PGF₂, a prostaglandin analog according to claim
 124. 126. A prostaglandin analog according to claim 118 wherein g is one.
 127. A prostaglandin analog according to claim 126, wherein at least one of R₃ and R₄ is methyl.
 128. A prostaglandin analog according to claim 127, wherein R₃ and R₄ are both methyl.
 129. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-16-methyl-16-phenyl-18,19,20-trinor-13,14-didehydro-PGF₂, a prostaglandin analog according to claim
 128. 130. A prostaglandin analog according to claim 126, wherein at least one of R₃ and R₄ is fluoro.
 131. A prostaglandin analog according to claim 130, wherein R₃ and R₄ are both fluoro.
 132. A prostaglandin analog according to claim 131, wherein R₅ is methyl.
 133. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-15-methyl-16,16-difluoro-16-phenyl-17,18,19,20-tetranor-13,14-didehydro-PGF₂, a prostaglandin analog according to claim
 132. 134. A prostaglandin analog according to claim 131, wherein R₅ is hydrogen.
 135. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-16,16-difluoro-16-phenyl-17,18,19,20-tetranor-13,14-didehydro-PGF₂, a prostaglandin analog according to claim
 134. 136. A prostaglandin analog according to claim 126, wherein R₃ and R₄ are both hydrogen.
 137. A prostaglandin analog according to claim 136, wherein R₅ is methyl.
 138. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-15-methyl-16-phenyl-17,18,19,20-tetranor-13,14-didehydro-PGF₂, a prostaglandin analog according to claim
 137. 139. A prostaglandin analog according to claim 136, wherein R₅ is hydrogen.
 140. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-16-phenyl-17,18,19,20-tetranor-13,14-didehydro-PGF₂, a prostaglandin analog according to claim
 139. 141. A prostaglandin analog according to claim 1, wherein Y₁ is trans--CH═CH--.
 142. A prostaglandin analog according to claim 141, wherein ##STR15##
 143. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-3,7-inter-m-phenylene-16-phenyl-4,5,6,17,18,19,20-heptanor-PGF₁, a prostaglandin analog according to claim
 142. 144. A prostaglandin analog according to claim 141, wherein ##STR16##
 145. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-3,7-inter-m-phenylene-3-oxa-16-phenyl-4,5,6,17,18,19,20-heptanor-PGF₁, a prostaglandin analog according to claim
 144. 146. A prostaglandin analog according to claim 141, wherein Z₁ is cis--CH₂ --CH═CH--(CH₂)_(g) --CH₂ --.
 147. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-cis-4,5-didehydro-16-phenyl-17,18,19,20-tetranor-PGF₁, a prostaglandin analog according to claim
 146. 148. A prostaglandin analog according to claim 141, wherein Z₁ is --CH₂ --O--CH₂ --(CH₂)_(h) --CH₂ --.
 149. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-5-oxa-16-phenyl-17,18,19,20-tetranor-PGF₁, a prostaglandin analog according to claim
 148. 150. A prostaglandin analog according to claim 141, wherein Z₁ is --C.tbd.C--CH₂ --(CH₂)_(g) --CH₂ --.
 151. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-4,5-didehydro-16-phenyl-17,18,19,20-tetranor-PGF₂, a prostaglandin analog according to claim
 150. 152. A prostaglandin analog according to claim 141, wherein Z₁ is --CH₂ --C.tbd.C--(CH₂)_(g) --CH₂ --.
 153. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-4,4,5,5-tetradehydro-16-phenyl-17,18,19,20-tetranor-PGF₁, a prostaglandin analog according to claim
 152. 154. A prostaglandin analog according to claim 141, wherein Z₁ is --(CH₂)₃ --(CH₂)_(g) --CH₂ --.
 155. A prostaglandin analog according to claim 154, wherein M₁ is ##STR17##
 156. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-15-epi-16-phenyl-17,18,19,20-tetranor-PGF₁, a prostaglandin analog according to claim
 155. 157. A prostaglandin analog according to claim 154, wherein M₁ is ##STR18##
 158. A prostaglandin analog according to claim 157, wherein s is zero or one and T is chloro, fluoro, or trifluoromethyl.
 159. A prostaglandin analog according to claim 158, wherein g is
 3. 160. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-2a,2b-dihomo-15-methyl-16-phenyl-17,18,19,20-tetranor-PGF₁, a prostaglandin analog according to claim
 159. 161. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-2a,2b-dihomo-16-phenyl-17,18,19,20-tetranor-PGF.sub.1, a prostaglandin analog according to claim
 159. 162. A prostaglandin analog according to claim 158, wherein g is one.
 163. A prostaglandin analog according to claim 162, wherein at least one of R₃ and R₄ is methyl.
 164. A prostaglandin analog according to claim 173, wherein R₃ and R₄ are both methyl.
 165. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-16-methyl-16-phenyl-18,19,20-trinor-PGF₁, a prostaglandin analog according to claim
 164. 166. A prostaglandin analog according to claim 162, wherein at least one of R₃ and R₄ is fluoro.
 167. A prostaglandin analog according to claim 166, wherein R₃ and R₄ are both fluoro.
 168. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-16,16-difluoro-16-phenyl-17,18,19,20-tetranor-PGF₁, a prostaglandin analog according to claim
 167. 169. A prostaglandin analog according to claim 162, wherein R₃ and R₄ are both hydrogen.
 170. A prostaglandin analog according to claim 169, wherein R₅ is methyl.
 171. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-15-methyl-16-phenyl-17,18,19,20-tetranor-PGF₁, a prostaglandin analog according to claim
 170. 172. A prostaglandin analog according to claim 169, wherein R₅ is hydrogen.
 173. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-16-phenyl-17,18,19,20-tetranor-PGF₁, a prostaglandin analog according to claim
 172. 174. A prostaglandin analog accordin to claim 141, wherein Z₁ is cis--CH═CH--CH₂ --(CH₂)_(g) --CH₂ --.
 175. A prostaglandin analog according to claim 174, wherein M₁ is ##STR19##
 176. A prostaglandin analog according to claim 175, wherein s is zero or one and T is chloro, fluoro, or trifluoromethyl.
 177. A prostaglandin analog according to claim 176, wherein g is
 3. 178. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-2a,2b-dihomo-15-epi-15-methyl-16-phenyl-17,18,19,20-tetranor-PGF₂, a prostaglandin analog according to claim
 177. 179. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-2a,2b-dihomo-15-epi-16-phenyl-17,18,19,20-tetranor-PGF.sub.2, a prostaglandin analog according to claim
 177. 180. A prostaglandin analog according to claim 176, wherein g is one.
 181. A prostaglandin analog according to claim 180, wherein at least one of R₃ and R₄ is methyl.
 182. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-15-epi-16-methyl-16-phenyl-18,19,20-trinor-PGF₂, a prostaglandin analog according to claim
 181. 183. A prostaglandin analog according to claim 180, wherein at least one of R₃ and R₄ is fluoro.
 184. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-15-epi-16,16-difluoro-16-phenyl-17,18,19,20-tetranor-PGF₂, a prostaglandin analog according to claim
 183. 185. A prostaglandin analog according to claim 180, wherein R₃ and R₄ are both hydrogen.
 186. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-15-epi-15-methyl-16-phenyl-17,18,19,20-tetranor-PGF₂, a prostaglandin analog according to claim
 185. 187. A prostaglandin analog according to claim 174, wherein M₁ is ##STR20##
 188. A prostaglandin analog according to claim 187, wherein s is zero or one and T is chloro, fluoro, or trifluoromethyl.
 189. A prostaglandin analog according to claim 188, wherein g is
 3. 190. A prostaglandin analog according to claim 189, wherein at least one of R₃ and R₄ is methyl.
 191. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-2a,2b-dihomo-16-methyl-16-phenyl-18,19,20-trinor-PGF.sub.2, a prostaglandin analog according to claim
 190. 192. A prostaglandin analog according to claim 189, wherein at least one of R₃ and R₄ is fluoro.
 193. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-2a,2b-dihomo-16,16-difluoro-16-phenyl-17,18,19,20-tetranor-PGF₂, a prostaglandin analog according to claim
 190. 194. A prostaglandin analog according to claim 189, wherein R₃ and R₄ are both hydrogen.
 195. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-2a,2b-dihomo-15-methyl-16-phenyl-17,18,19,20-tetranor-PGF₂, a prostaglandin analog according to claim
 194. 196. A prostaglandin analog according to claim 188, wherein g is one.
 197. A prostaglandin analog according to claim 196, wherein at least one of R₃ and R₄ is methyl.
 198. A prostaglandin analog according to claim 197, wherein R₃ and R₄ are both methyl.
 199. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-16-methyl-16-phenyl-18,19,20-trinor-PGF₂, a prostaglandin analog according to claim
 198. 200. A prostaglandin analog according to claim 196, wherein at least one of R₃ and R₄ is fluoro.
 201. A prostaglandin analog according to claim 200, wherein R₃ and R₄ are both fluoro.
 202. A prostaglandin analog according to claim 201, wherein R₅ is methyl.
 203. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-15-methyl-16,16-difluoro-16-phenyl-17,18,19,20-tetranor-PGF₂, a prostaglandin analog according to claim
 202. 204. A prostaglandin analog according to claim 201, wherein R₅ is hydrogen.
 205. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-16,16-difluoro-16-phenyl-17,18,19,20-tetranor-PGF₂, a prostaglandin analog according to claim
 204. 206. A prostaglandin analog according to claim 204, wherein R₃ and R₄ are both hydrogen.
 207. A prostaglandin analog according to claim 206, wherein R₅ is methyl.
 208. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-15-methyl-16-phenyl-17,18,19,20-tetranor-PGF₂, a prostaglandin analog according to claim
 207. 209. A prostaglandin analog according to claim 206, wherein R₅ is hydrogen.
 210. 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-16-phenyl-17,18,19,20-tetranor-PGF₂, a prostaglandin analog according to claim
 209. 